5-chloro-2-(trifluoromethyl)-1,8-Naphthyridine → HCID 10110736, compound

HRID 1061794Notes

Reaction equation

HRID 1061794 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:12]([F:15])([F:14])[F:13])=[N:7]2.[F:16][C:17]1[CH:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][C:18]=1[C:32]1[CH:37]=[CH:36][N:35]=[CH:34][C:33]=1[F:38]>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:11]=[CH:10][N:9]=[C:8]3[C:3]=2[CH:4]=[CH:5][C:6]([C:12]([F:15])([F:14])[F:13])=[N:7]3)=[CH:19][C:18]=1[C:32]1[CH:37]=[CH:36][N:35]=[CH:34][C:33]=1[F:38]

Participants

3

Reactant 2

HCID 222852765-chloro-2-(trifluoromethyl)-1,8-NaphthyridineHCID 22285312HCID 22285312, compound

Product 1

HCID 10110736HCID 10110736, compoundYield 40%

Procedure

5-Chloro-2-trifluoromethyl[1,8]naphthyridine (50 mg, 0.22 mmol) was coupled to 4-[2-fluoro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-3-fluoropyridine (89 mg, 0.28 mmol) as described in Example 7 part g), affording 5-[4-fluoro-3-(3-fluoropyridin-4-yl)phenyl]-2-trifluoromethyl[1,8]naphthyridine (33 mg, 40%). δH (360 MHz, CDCl3) 7.43-7.49 (2H, m), 7.58-7.61 (3H, m), 7.86 (1H, d, J 8.8), 8.55 (2H, dd, J 6.0 and 2.1), 8.63 (1H, d, J 1.8), 9.30 (1H, d, J 4.2). m/z (ES+) 388 [MH]+.

Sources & evidence

ORD record
ord-706f0749b85242aaab9255dbf374d11f
Source dataset
uspto-grants-2005_11
Patent number
US06960598B2

Reaction notes

Loading…